Work

Imino‐λ3‐iodane and Catalytic Amount of I2‐Mediated Synthesis of N‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement

Year: 2020

Type: article

Abstract: A facile metal‐free [2,3]‐sigmatropic rearrangement reaction of allyl sulfides via N‐sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino‐λ3‐iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N‐allylsulfenamide compounds in moderate to good yields. Several N‐allylsulfenamide structures have been confirmed by single‐crystal X‐ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino‐λ3‐iodane and the sulfur atom, resulting in the formation of N‐sulfilimine species, followed by [2,3]‐sigmatropic rearrangement to form the N‐allylsulfenamide.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202000961